15958PathwayPhosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))Phosphatidylethanolamines (PE) are a class of phospholipids that incorporate a phosphoric acid headgroup into a diacylglycerol backbone. They are the second most abundant phospholipid in eukaryotic cell membranes, and contrary to phosphatidylcholine, it is concentrated with phosphatidylserine in the cell membrane's inner leaflet. In Homo sapiens, there exist two phosphatidylethanolamine biosynthesis pathways. In the visualization, all enzymes that are dark green in colour are membrane-localized. The first pathway synthesizes phosphatidylethanolamine from ethanolamine via the Kennedy pathway. First, the cytosol-localized enzyme choline/ethanolamine kinase catalyzes the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. Phosphatidylethanolamine is also synthesized from phosphatidylserine at the mitochondrial inner membrane by phosphatidylserine decarboxylase. Phosphatidylserine, itself, is synthesized using a base-exchange reaction with phosphatidylcholine. This reaction is catalyzed by phosphatidylserine synthase which is located in the endoplasmic reticulum membrane.MetabolicPW016148CenterPathwayVisualizationContext1643221962100#000099PathwayVisualization1590315958Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))Phosphatidylethanolamines (PE) are a class of phospholipids that incorporate a phosphoric acid headgroup into a diacylglycerol backbone. They are the second most abundant phospholipid in eukaryotic cell membranes, and contrary to phosphatidylcholine, it is concentrated with phosphatidylserine in the cell membrane's inner leaflet. In Homo sapiens, there exist two phosphatidylethanolamine biosynthesis pathways. In the visualization, all enzymes that are dark green in colour are membrane-localized. The first pathway synthesizes phosphatidylethanolamine from ethanolamine via the Kennedy pathway. First, the cytosol-localized enzyme choline/ethanolamine kinase catalyzes the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. Phosphatidylethanolamine is also synthesized from phosphatidylserine at the mitochondrial inner membrane by phosphatidylserine decarboxylase. Phosphatidylserine, itself, is synthesized using a base-exchange reaction with phosphatidylcholine. This reaction is catalyzed by phosphatidylserine synthase which is located in the endoplasmic reticulum membrane.Metabolic122002Phosphatidylcholine BiosynthesisSubPathway210714163Compound491939022791820Alatorre-Cobos F, Cruz-Ramirez A, Hayden CA, Perez-Torres CA, Chauvin AL, Ibarra-Laclette E, Alva-Cortes E, Jorgensen RA, Herrera-Estrella L: Translational regulation of Arabidopsis XIPOTL1 is modulated by phosphocholine levels via the phylogenetically conserved upstream open reading frame 30. J Exp Bot. 2012 Sep;63(14):5203-21. doi: 10.1093/jxb/ers180. Epub 2012 Jul 12.15958Pathway1939110893425Henneberry AL, Wistow G, McMaster CR: Cloning, genomic organization, and characterization of a human cholinephosphotransferase. J Biol Chem. 2000 Sep 22;275(38):29808-15.15958Pathway1939219915674Gallego-Ortega D, Ramirez de Molina A, Ramos MA, Valdes-Mora F, Barderas MG, Sarmentero-Estrada J, Lacal JC: Differential role of human choline kinase alpha and beta enzymes in lipid metabolism: implications in cancer onset and treatment. PLoS One. 2009 Nov 12;4(11):e7819. doi: 10.1371/journal.pone.0007819.15958Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404Cardiomyocyte CL:00007468Beta cellCL:00006397Epithelial CellCL:000006610Glial cellCL:00001251Homo sapiens9606EukaryoteHuman4Arabidopsis thaliana3702EukaryoteThale cress38homo sapiens9608Eukaryote2Bacteria2ProkaryoteBacteria3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse17Rattus norvegicus10116EukaryoteRat19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel51Picea sitchensis3332EukaryoteSitka spruce5CytoplasmGO:000573713Endoplasmic ReticulumGO:00057831CytosolGO:00058293Mitochondrial MatrixGO:000575914Mitochondrial Outer MembraneGO:00057412MitochondrionGO:000573915NucleusGO:00056344PeroxisomeGO:00057777Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577831Periplasmic SpaceGO:000562011Extracellular SpaceGO:000561535chloroplastGO:000950712Mitochondrial Inner MembraneGO:000574319sarcoplasmic reticulumGO:001652924Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032539Mitochondrial membraneGO:003196625Golgi apparatusGO:000579426Golgi apparatus membraneGO:00001392Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:0001102741128StomachBTO:0001307155264Adrenal MedullaBTO:00000497188511PW_BS0000082491341PW_BS000024151141PW_BS0001512111PW_BS0000022761381PW_BS0000244311PW_BS00000416212PW_BS000016221411PW_BS00002213121PW_BS0000133211515PW_BS0000325411PW_BS000005397113PW_BS0000393211PW_BS000003181311PW_BS000018101711PW_BS00001049711PW_BS00004914101PW_BS0000145811411PW_BS000058592711PW_BS00005927151PW_BS00002746114PW_BS00004629111PW_BS0000296618518PW_BS00006672513PW_BS000072612517PW_BS0000615181PW_BS000051231511PW_BS000023311511PW_BS000031918511PW_BS000091541315PW_BS000054892PW_BS000089261115PW_BS000026711PW_BS000007971521PW_BS000097100521PW_BS0001001041431PW_BS000104101531PW_BS0001011115121PW_BS0001111122121PW_BS000112103331PW_BS000103117131PW_BS0001171181171PW_BS0001181203171PW_BS00012012915121PW_BS0001291321121PW_BS0001321333121PW_BS0001331355171PW_BS00013510813PW_BS00010814315191PW_BS0001431465191PW_BS000146107313PW_BS0001071471241PW_BS0001471553241PW_BS0001551613181PW_BS00016116611PW_BS00016617315381PW_BS0001731765381PW_BS0001761783211PW_BS000178188118PW_BS0000241601181PW_BS00016019914181PW_BS000024205561PW_BS000024206261PW_BS00002421013181PW_BS0000242137181PW_BS0000242111018PW_BS0000241985181PW_BS0000242164181PW_BS0000242171518PW_BS00002421815181PW_BS0000241632181PW_BS000163222341PW_BS0000241901118PW_BS0000242253541PW_BS00002425214381PW_BS0000242752381PW_BS0000242771218PW_BS00002417018PW_BS0001702811251PW_BS0000241644PW_BS0001642513381PW_BS0000242851041PW_BS000024226441PW_BS0000242905491PW_BS0000242231241PW_BS0000243081011PW_BS00002421217181PW_BS00002415111PW_BS000015471914PW_BS000047943PW_BS000094171211PW_BS000017422411PW_BS0000427028511PW_BS000070105113PW_BS0001051572241PW_BS00015715924PW_BS00015915284PW_BS0001521873118PW_BS000024219314PW_BS00002422014PW_BS00002416212181PW_BS000162224241PW_BS0000241951318PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000242881441PW_BS00002430635511PW_BS0000243093911PW_BS00002420175110PW_BS000024202711110PW_BS000024711113PW_BS0000711192171PW_BS0001191371117PW_BS00013711PW_BS000001204111PW_BS000020432511PW_BS000043562611PW_BS00005696EthanolamineHMDB00149Ethanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.141-43-5C0018970016000ETHANOL-AMINE13835336DB03994NCCOC2H7NOInChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2HZAXFHJVJLSVMW-UHFFFAOYSA-N2-aminoethan-1-ol61.083161.0527638511.142ethanolamine01FDB0007691-amino-2-hydroxyethane;2-amino-1-ethanol;2-aminoethanol;2-aminoethyl alcohol;2-ethanolamine;2-hydroxyethanamine;2-hydroxyethylamine;Aethanolamin;Aminoethanol;Colamine;Envision conditioner pdd 9020;Ethanolamine;Ethylolamine;Glycinol;H-glycinol;Mea;Monoaethanolamin;Monoethanolamine;Olamine;B-aminoethanol;B-aminoethyl alcohol;B-ethanolamine;B-hydroxyethylamine;Beta-aminoethanol;Beta-aminoethyl alcohol;Beta-ethanolamine;Beta-hydroxyethylamine;Eta;2-amino-ethanol;2-aminoethan-1-ol;Hea;β-aminoethanol;β-aminoethyl alcohol;β-ethanolamine;β-hydroxyethylaminePW_C0000961564891462491217415115326215381276414Adenosine triphosphateHMDB00538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C0004149221460826616414224781373332799593439976321051821121021464921561421605824055924342727264628122930296631637236166136175143992344743147689148645450328950352651557520597521510052501045291101531311153461125390103540611754301185443120554212955561325569133560313556211085846143585414658761075897147592415160481556109161623016664301736438176649317868391886870160697619971572057184206720921072252137229211729819873022167390217740821874321637481222749919081862259184252117042761172827511847277119031701201028112039164121152511217828512578226126912901326422315327308149O-PhosphoethanolamineHMDB00224Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524, 8588821, 11566853).1071-23-4C00346101517553PHOSPHORYL-ETHANOLAMINE990NCCOP(O)(O)=OC2H8NO4PInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)SUHOOTKUPISOBE-UHFFFAOYSA-N(2-aminoethoxy)phosphonic acid141.063141.019094261-0.743phosphorylethanolamine0-1FDB0219112-amino-ethanol dihydrogen phosphate;2-amino-ethanol dihydrogen phosphate (ester);2-amino-ethanol phosphate;2-aminoethanol o-phosphate;2-aminoethyl dihydrogen phosphate;2-aminoethyl dihydrogen phosphate (acd/name 4.0);2-aminoethyl phosphate;Colamine acid phosphate;Colamine phosphate;Colamine phosphoric acid;Colaminephosphoric acid;Colaminphosphoric acid;Eap;Ethanolamine o-phosphate;Ethanolamine acid phosphate;Ethanolamine phosphate;Mono(2-aminoethyl) phosphate;Monoaminoethyl phosphate;O-phosphocolamine;O-phosphoethanolamine;O-phosphorylethanolamine;Ope;Petn;Phosphoethanolamine;Phosphonoethanolamine;Phosphoric acid 2-aminoethyl phenyl ester;Phosphoryethanolamine;Phosphorylethanolamine;Pe;Pea;Phosphoryl-ethanolamine;2-amino-ethanol dihydrogen phosphoric acid;2-aminoethyl dihydrogen phosphoric acid;2-amino-ethanol phosphoric acid;Colaminphosphate;Ethanolamine acid phosphoric acid;Ethanolamine o-phosphoric acid;Ethanolamine phosphoric acid;Mono(2-aminoethyl) phosphoric acid;Monoaminoethyl phosphoric acid;Phosphate 2-aminoethyl phenyl ester;Ethamp;O-phosphonatoethanaminiumPW_C000149211810497887214212121792851532830815355151153762153822761034Adenosine diphosphateHMDB01341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C00103423413484152248213801596315978310611415182190149210418211310216158240859243527272847273646285529316572363561440023447631477091503626515775208975217100531511153491125392103544612055441295572133562410857411175764101584914358561465878107589914759261516050155611116162311666433173644017664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511707276117302751185127711905170120132811211725112180285132622231532930840034Hydrogen IonHMDB59597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C04003421546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552499174251117112751191516412015281121812851224628612266287125212271325722313325294153303081538327657Cytidine triphosphateHMDB00082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C00005742723115082718257661015800108707718875931609137195914221312194164125102881528515115317249153422215374183475917170PyrophosphateHMDB00250In chemistry, the anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonatooxy)phosphonate173.9433173.9119253780diphosphate-4-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170122354638429237353288222121731620492410592815294175144868545034895252104529410154091175424103543311854581205548111555913255841335606135565510858791076239166697819970731887134163727216073121987318213827515182832109186252118691611200222212041164123152251232324912512288125792261269529015219306153751834760171201CDP-EthanolamineHMDB01564Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond.3036-18-8C0057012372716732CDP-ETHANOLAMINE110296NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=OC11H20N4O11P2InChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1WVIMUEUQJFPNDK-PEBGCTIMSA-N[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](2-aminoethoxy)phosphinic acid446.2442446.060380526-1.536cdp ethanolamine0-1FDB022691Cdp ethanolamine;Cdp-ethanolamine;Cdpethanolamine;Cytidine diphosphate ethanolamine;Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) esterPW_C00120133841815290288153432240895494163PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))HMDB08115PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the eicsoatetraenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.C0015753478767 PHOSPHATIDYLCHOLINE24766777CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC46H82NO8PInChI=1S/C46H82NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14,16,20-22,24-25,27,44H,6-7,9,11-13,15,17-19,23,26,28-43H2,1-5H3/b10-8-,16-14-,22-20-,24-21-,27-25-/t44-/m1/s1SWOKEJBWARJLGN-ORKYUJCWSA-N(2-{[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium808.1189807.577805117-7.480lecithin00FDB0253051-oleoyl-2-eicsoate;1-oleoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine;1-oleoyl-2-eicsoic acid;Gpcho(18:1/20:4);Gpcho(18:1n9/20:4n3);Gpcho(18:1w9/20:4w3);Gpcho(38:5);Lecithin;Pc aa c38:5;Pc(18:1/20:4);Pc(18:1n9/20:4n3);Pc(18:1w9/20:4w3);Pc(38:5);Phosphatidylcholine(18:1/20:4);Phosphatidylcholine(18:1n9/20:4n3);Phosphatidylcholine(18:1w9/20:4w3);Phosphatidylcholine(38:5)PW_C0041631715649171573092298118120L-SerineHMDB00187Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).56-45-1C00065595117115SER5736DB00133N[C@@H](CO)C(O)=OC3H7NO3InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1MTCFGRXMJLQNBG-REOHCLBHSA-N(2S)-2-amino-3-hydroxypropanoic acid105.0926105.0425930950.663L-serine00FDB012739(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionatePW_C0001203448181022617456421075643108588410560111476907163708620170872027090717091727202160743837443157444166752222483572259154249121731511262518153794965CholineHMDB00097Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine e to methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.62-49-7C0011430515354CPD-563299DB00122C[N+](C)(C)CCOC5H14NOInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1OEYIOHPDSNJKLS-UHFFFAOYSA-N(2-hydroxyethyl)trimethylazanium104.1708104.107539075-1.591choline11FDB000710(2-hydroxyethyl)trimethyl ammonium;(2-hydroxyethyl)trimethylammonium;(beta-hydroxyethyl)trimethylammonium;2-hydroxy-n,n,n-trimethyl-ethanaminium;2-hydroxy-n,n,n-trimethylethanaminium;Bilineurine;Biocolina;Biocoline;Choline;Choline cation;Choline ion;Cholinum;Hepacholine;Hormocline;Lipotril;N,n,n-trimethylethanol-ammonium;N,n,n-trimethylethanolammonium;Neocolina;Paresan;N-trimethylethanolamine;TrimethylethanolaminePW_C00006556235641556581497145612119561913768497121851511219716412278226153392153804960817PS(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))PS(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants, and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups (i.e. the phosphate moiety, the amino group and the carboxyl group). As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have a palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.C02737632348118303L-1-PHOSPHATIDYL-SERINE13628254DB00144[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=OC44H76NO10PInChI=1S/C44H76NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-19,21-22,24,40-41H,3-4,6,8-10,12,14-16,20,23,25-39,45H2,1-2H3,(H,48,49)(H,50,51)/b7-5-,13-11-,19-17-,21-18-,24-22-/t40-,41+/m1/s1YEPDLFVZBAYNRO-ATQPJVMYSA-N(2S)-2-amino-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid810.063809.520684649-7.063(2S)-2-amino-3-{[hydroxy((2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propanoic acid0-11-oleoyl-2-eicosatetraenoyl-sn-glycero-3-phosphoserine ;PS(18:1/20:4) ;PS(18:1n9/20:4n3) ;PS(18:1w9/20:4w3) ;PS(38:5) ;Pser(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) ;Pser(18:1/20:4) ;Pser(18:1n9/20:4n3) ;Pser(18:1w9/20:4w3) ;Pser(38:5) ;Phosphatidylserine(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) ;Phosphatidylserine(18:1/20:4) ;Phosphatidylserine(18:1n9/20:4n3) ;Phosphatidylserine(18:1w9/20:4w3) ;Phosphatidylserine(38:5)PW_C06081717158309229824922983175118PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))HMDB09070PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the eicsoatetraenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.C0035053479651L-1-PHOSPHATIDYL-ETHANOLAMINE24768535[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC43H76NO8PInChI=1S/C43H76NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44)39-49-42(45)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-19,21-22,24,41H,3-4,6,8-10,12,14-16,20,23,25-40,44H2,1-2H3,(H,47,48)/b7-5-,13-11-,19-17-,21-18-,24-22-/t41-/m1/s1ZYMZKMQPPJPQHY-COHGUQLJSA-N(2-aminoethoxy)[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid766.0392765.530854925-7.0222-aminoethoxy(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphinic acid00C003501-oleoyl-2-eicsoate;1-oleoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphoethanolamine;1-oleoyl-2-eicsoic acid;Gpetn(18:1/20:4);Gpetn(18:1n9/20:4n3);Gpetn(18:1w9/20:4w3);Gpetn(38:5);Pe(18:1/20:4);Pe(18:1n9/20:4n3);Pe(18:1w9/20:4w3);Pe(38:5);Phophatidylethanolamine(18:1/20:4);Phophatidylethanolamine(18:1n9/20:4n3);Phophatidylethanolamine(18:1w9/20:4w3);Phophatidylethanolamine(38:5)PW_C00511817154491715530922984171316Carbon dioxideHMDB01967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-Nmethanedione44.009543.9898292440.630carbon dioxide00DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C0013165081211204448013503186403677316952080651133431638491745225511731447052831035320111575010857711015968100602615560781616471178663710769221907017160703516370611887163205730819873332137461222753021082152258223151915824992122511169527511713276118492771190817012464226126882903280DG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/0:0)HMDB07229DG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/0:0), in particular, consists of one chain of oleic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the eicsoatetraenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.C0016553478094DIACYLGLYCEROL24766000[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC41H70O5InChI=1S/C41H70O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-19,21-22,24,39,42H,3-4,6,8-10,12,14-16,20,23,25-38H2,1-2H3/b7-5-,13-11-,19-17-,21-18-,24-22-/t39-/m0/s1CDIDDLXSXXDECX-YGTYKICOSA-N(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate642.9915642.52232535-7.701diacylglycerol00FDB0244221-oleoyl-2-eicsoate;1-oleoyl-2-eicsoatetraenoyl-sn-glycerol;1-oleoyl-2-eicsoic acid;Dag(18:1/20:4);Dag(18:1n9/20:4n3);Dag(18:1w9/20:4w3);Dag(38:5);Dg(18:1/20:4);Dg(18:1n9/20:4n3);Dg(18:1w9/20:4w3);Dg(38:5);Diacylglycerol;Diacylglycerol(18:1/20:4);Diacylglycerol(18:1n9/20:4n3);Diacylglycerol(18:1w9/20:4w3);Diacylglycerol(38:5);DiglyceridePW_C003280171534964Cytidine monophosphateHMDB00095Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].63-37-6C00055613117361CMP5901NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC9H14N3O8PInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1IERHLVCPSMICTF-XVFCMESISA-N{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid323.1965323.051850951-1.305cytidine monophosphate0-2FDB0118825'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acidPW_C00006411518251214273423386184972565768101580210870791887595160914724991512249257195121961641221015115274285153363081537349348151711846Choline kinase alphaP35790Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.HMDBP00778CHKA11q13.2BC03647112.7.1.32;2.7.1.8215351225487276697Ethanolamine-phosphate cytidylyltransferaseQ99447Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
HMDBP00738PCYT217q25.3CH47109912.7.7.1441298153704911850Phosphatidylserine synthase 1P48651Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.HMDBP02190PTDSS18q22BC00439012.7.8.29;2.7.8.-153774925476181860Phosphatidylserine decarboxylase proenzymeQ9UG56HMDBP02255PISD22q12.2BC00931514.1.1.65156910153711711849Choline/ethanolaminephosphotransferase 1Q9Y6K0Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.HMDBP03349CEPT11p13.3AF13886212.7.8.1;2.7.8.2153724925475185654choline/ethanolamine kinase1PW_P0056541312411846153522970Ethanolamine-phosphate cytidylyltransferase1PW_P000970109669715663phosphatidylserine synthase1PW_P005663131331185015378495662phosphatidylserine decarboxylase1PW_P0056621313218601535735657choline/ethanolaminephosphotransferase1PW_P0056571312711849153561849890PW_R089556Right158466961Compound1584674141Compound1584681491Compound15846910341Compound158470400341Compound4001556542.7.1.8249900PW_R089566Right158512571Compound1585131491Compound1585141701Compound15851512011Compound400259702.7.7.1455175PW_R094840Right17961641631Compound1796171201Compound179618651Compound179619608171Compound4530056632.7.8.-51244PW_R090909Right163893608171Compound16389451181Compound16389513161Compound41369566251242PW_R090907Right16388412011Compound16388532801Compound163886641Compound16388751181Compound4136756578202489623false178839910100100820249414242false173833410503082025014923false1338396101001108202511034243false143833410503082025240034255false142421110787882025357183false1466535101001108202541701845false14638381063438202551201493false1333874101001108202564163493false306130410100100820257120493false35614541010010082025865493false70614521010010082025960817493false81113021010010082026060817493false8101695101001008202615118493false12601691101001008202625118493false126212551010010082026313161752false121118211078788202643280493false11939441010010082026564493false14571210101001103647151184626false15334118protein1608036471669749119false12326958subunit16080364717118504999false50613198protein1507036471818601799false101017078protein15070364719118494999false123610908protein15070256935565415903236388936471525693697015903493638903647162569375663159034936389136471725693856621590317363892364718256939565715903493638933647191166478M1310 1691 C1311 1631 1312 1390 1312 1355 83false18trueM 858.5 1398.9903810567666 L 851 1386 L 843.5 1398.9903810567666falsetrueM 1468.7175177365857 1931.8864401445276 L 1476 1945 L 1483.7154348371798 1932.1364054295375false1166479M861 1402 C861 1422 859 1674 860 1695 83false18trueM 269.06440098298674 1401.611518094107 L 284 1403 L 277.73466109469183 1389.371150877582falsefalsefalse1166480M1788 449 C1758 449 1723 451 1693 451 5false181166481M1738 349 C1740 406 1723 451 1693 451 5false181166482M1438 451 C1468 451 1503 451 1533 451 5false18trueM 597.9468550441649 17.26155629629604 L 583 16 L 589.3808877211858 29.575134323078345false1166483M1488 349 C1488 417 1503 451 1533 451 5false18trueM 597.9468550441649 17.26155629629604 L 583 16 L 589.3808877211858 29.575134323078345false1166484M1502 250 C1499 350 1503 451 1533 451 5false18trueM 597.9468550441649 17.26155629629604 L 583 16 L 589.3808877211858 29.575134323078345false1166485M1516 645 C1448 646 1312 665 1312 695 5false181166486M1388 506 C1388 525 1387 539 1387 559 C1367 560 1329 558 1310 558 C1310 578 1311 668 1312 695 5false18trueM 843.0243431731823 703.2961069675144 L 851 716 L 858.0140656796838 702.7409320598663false1166487M1494.5 838 C1388.5 837 1312 805 1312 775 5false18trueM 464.94685504416486 495.261556296296 L 450 494 L 456.38088772118584 507.5751343230783false1166488M1383 874 C1383 853 1382 860 1383 840 C1362 840 1332 839 1311 840 C1311 820 1311 796 1312 775 5false18trueM 464.94685504416486 495.261556296296 L 450 494 L 456.38088772118584 507.5751343230783false1166489M406 1354 C436 1354 476 1354 506 1354 5false181166490M306 1354 C286 1354 313 1352 292 1353 C272 1353 274 1331 273 1308 C273 1287 273 1206 273 1184 5false18trueM 293.0096189432334 1361.5 L 306 1354 L 293.0096189432334 1346.5false1166491M456 1504 C455 1448 476 1354 506 1354 5false181166492M706 1502 C705 1442 686 1354 656 1354 5false18trueM 25.946855044164835 1121.261556296296 L 11 1120 L 17.380887721185843 1133.5751343230784false1166493M811 1352 C781 1352 686 1354 656 1354 5false18trueM 25.946855044164835 1121.261556296296 L 11 1120 L 17.380887721185843 1133.5751343230784false1166494M910 1745 C940 1745 980 1742 1010 1742 5false181166495M1260 1741 C1230 1741 1190 1742 1160 1742 5false18trueM 511.94685504416486 1283.261556296296 L 497 1282 L 503.38088772118584 1295.5751343230784false1166496M1211 1860 C1211 1781 1190 1742 1160 1742 5false18trueM 511.94685504416486 1283.261556296296 L 497 1282 L 503.38088772118584 1295.5751343230784false1166497M1383 984 C1383 1004 1383 1020 1383 1040 C1364 1040 1329 1039 1309 1039 C1309 1058 1311 1072 1311 1090 5false18trueM 1542.5 1064.0096189432334 L 1550 1077 L 1557.5 1064.0096189432334false1166498M1243 1044 C1279 1049 1311 1060 1311 1090 5false181166499M1507 1210 C1434 1207 1311 1190 1311 1160 5false18trueM 511.94685504416486 882.261556296296 L 497 881 L 503.38088772118584 894.5751343230784false1166500M1312 1255 C1312 1225 1311 1190 1311 1160 5false18trueM 511.94685504416486 882.261556296296 L 497 881 L 503.38088772118584 894.5751343230784false268465159034989010474128202481166480Left10474138202491166481Left10474148202501166482Right10474158202511166483Right10474168202521166484Right22753240015256935268466159034990010474178202531166485Left10474188202501166486Left10474198202541166487Right10474208202551166488Right22753340025256936268467159035517510474218202561166489Left10474228202571166491Left10474238202581166492Right10474248202591166493Right22753440045256937268468159035124410474258202601166494Left10474268202611166495Right10474278202631166496Right22753540040256938268469159035124210474288202551166497Left10474298202641166498Left10474308202651166499Right10474318202621166500Right2275364003825693921361220021590314false198111416195708202561166490Right266061166478266071166479566663055401.01.0-902328036056667176714990.90.99011490240114960M248 1628.6666259765625 C317 1628.6666259765625 1340 1626.6666259765625 1424 1627.6666259765625 84false60.00.0114961M125 225 C125 175 175 125 225 125 C730 125 1386 125 1891 125 C1941 125 1991 175 1991 225 C1991 754 1991 1442 1991 1971 C1991 2021 1941 2071 1891 2071 C1386 2071 730 2071 225 2071 C175 2071 125 2021 125 1971 C125 1442 125 754 125 225 1true61866.01946.0114962M248 1746 C304 1746 1344 1742 1424 1742 84false61176.04.0114963M1291 605 C1292 650 1289 1197 1291 1280 C1292 1338 1238 1355 1183 1351 C1121 1353 373 1349 306 1350 C264 1355 273 1277 273 1224 C273 1164 272 705 272 605 91false61019.0746.09586515Endoplasmic Reticulum Membrane10021309201.01.0160159586615Mitochondrial Outer Membrane2571581201.01.0160159586715Cytosol1715683201.01.0160159586815Endoplasmic Reticulum Lumen330629201.01.0160159586915Mitochondrial Intermembrane Spance2551641201.01.0160159587015Mitochondrial Matrix2551767201.01.0160159587115Mitochondrial Inner Membrane2551702201.01.01601555758440393247604131713764#FFEEDE41070772557591584163624716021425194340#FFEBEB41178341